Gasoline and method of making the same



Patented Sept. 8, 1936 I GASOLINE AND METHOD OF MAKING THE SAME Harry T.Bennett and Le Roy G. Story, Tulsa, Okla., assignors, by mesneassignments, to Gasoline Antioxidant Company, Wilmington, Del., acorporation of Delaware No Drawing. Application January 16, 1928, SerialNo. 247,256. Renewed May 28, 1930 '19 Claims. (Cl. 44-9) This inventionrelates to gasoline and. more er-tendency to knock. It is important toprevent specifically to cracked gasoline. 'the formation of compoundswhich promote det- An important object of the invention is to onation incracked fuels, because it is by virtue produce a cracked gasoline whichwill-not den of the cracked or unsaturated nature of these posit aresidue of gum when vaporized. This is fuels that they have becomerecognized as antiaccomplished by treating fresh cracked gasoline knockgasolines. 5 so that it will neither deposit appreciable Our inventionovercomes the above mentioned amounts of gum when immediately evaporatedgum and detonation pro y inhibiting the nor accumulate said gum insolution when standreactions which produce m either When the ing instorage for long periods bef r cons mpfresh sample is evaporated or whenthe same ion. i

Another object is to produce a cracked gasoas previously Do Ou therebeing line which is stable in color, and this is accom= l e el i p w n tse p p y plished by preventing the formation of soluble preventing orinhibiting th a t ns w h p colored compounds in the gasoline onstanding. ce u w a supp ss the o atio of A further object is to preservethe anti-knock Compounds Causing detonation- 15 quality of the crackedgasoline i other words, The invention which we will hereafter describeto prevent the formation of luble detonating is concerned with theprevention of the reactions mpo ds, Sa d compounds being closely relatedwhich cause formation of gum rather than the to the gum constituents.remedy after the harm or effect has been caused,

product is allowed to age before evaporation; 10

With the foregoing objects in view, w W111 for we have found that oncethe gum has accu- 20 proceed to point out some of the undesirablemuleted in solutions it is Ve y diflielllt o remove characteristics ofcracked gasoline, how our inwithoutidrestie treatmeht- 0n the othervention overcomesthese undesirable characterhand. y Simple treatment ofthe fresh 8 istics, and finally compare our methods with line by 0111method before the harm s those previously used and point out theadvansuited, it s v asy t i h t the formation 25 tages of the methods wehave discovered. of um when the sample is v p t or e Cracked gasolineshave the property, even it is allowed to Standwhen freshly made, ofdepositing dark brown In order to overcome these undesirable propgummyresidues on surfaces from which they erties of cracked gasoline, We d toe E 3 are slowly evaporated. The composition of the line a Small q yOfeertain O a c comdeposit is not fully understood, but has becomepounds which We have discovered have e p pknown in the trade as gum andwill hereafter y f tin the f a i n of th undesirbe referred to by thisterm. The chemical reable The hetureehthe inhibiting caction producingthe gum is also not fully untiOh, whereby these organic o p u s film!-derstood, but we believe it is an oxidation retion to prevent theformation of um, is not 35 action eitherinternal or external; internaloxiclearly understood. but We characterize the 0 dation being thattaking place within the mapounds as inhibitors, antioxidants, e vOatterial itself, and external that caused by some eiyets, p y u e s- Wt the external power as oxygen fromthe air or the r p f an im formers whave found the rays of light. followingto be useful. 40

Another property commonly noted in gasolines Ortho-emihophenol.meto-eminophenol, par made from cracked products is formation of gumeminophenol. -be la op enol, beta-hyin solution which is evidenced by anincrease in droxyethylamihophenel, D t y a othe deposit left byevaporating a sample that Phenol, 5-benzylaminorz-firesoli has stood forsometime in comparison with that droxytohlene,5-emind-z-hydl'oxytoluehei Para, 45 formed by the original materialbefore aging. e a, r p e y nediamine, benzidine and The compounds whichhave the power'then of alpha naphthylamine. 'In order to classify theseproducing gum when the fresh sample is evapcompounds and not limitourselves to those speorated apparently proceed to form gum insolucified above, we prefer to distinguish them as) tion when the sameproduct is allowed tostand. at c m s d emihephenols and the de- Afurther property also related to gum is the Y S of th r e aSS-detonation characteristic. It is related in that The q i y of anti-gumformer required t a gasoline which has accumulated appreciableaccomplish our purpose varies somewhat, dependv quantities of gum insolution also shows a greating on the nature of the gasoline to betreated. 55

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We may use from two to fifty milligrams per icc cubic centimeters of thegasoline but we prefer to use approximately ten milligrams per 10o cubiccentimeters. This may be added to the gasoline directly or it may bepreviously dissolved in a solvent such as acetone, benzol or ether, etc,and then added, in solution, to the gasoline. The latter method has beenfound to be advantageous where the material is dimcultly dissolved.

In actual practice we prefer to treat a raw cracked gasoline direct fromthe still with approximately ten milligrams oi ortho-aminophenol percubic centimeters. By this treatment we have found that the treatedgasoline will deposit no appreciable gum when immediately evaporated orafter aging for long periods.

We wish to point out that our process is equally applicable to anygum-forming cracked gasoline, whether previously treated or not, as wellas the raw cracked gasoline mentioned in our preferred form. In fact ourprocess is valuable for treating fuels which have been acid treated orfiltered through fullers earth provided they tend to form gum onstorage, and also for blended fuels such as those containing productsnot strictly from petroleum among which may be mentioned those derivedfrom coal tar or shale oil.

Prior to our invention the methods used consisted in treating thecracked gasoline with poly Also the prior methods removed productswhichare valuable as fuel, especially for anti-knock purposes. Ourprocess on the other hand is simple in that any tank or similarequipment available in the ordinary refinery may be used for adding theanti-gum former and. the time required is of no important consideration;it is inexpensive, in that the quantity of treating material is verysmall since it enters into the reaction more in the nature of a catalystthan in quantitative proportions, and lastly no valuable constituents ofthe gasoline are lost as sludge.

' We claim: I

l. A substantially volatile mot'or fuel comprising cracked hydrocarbondistillates normally tending to deteriorate and develop gummy substanceson storage and containing an aminophenol in which an amino hydrogen hasbeen substituted by a hydrocarbon radical, in quantity suflicient toretard said gum formation.

2. The method of refining a motor fuel containing unsaturated crackedhydrocarbons which tend to form gum on storage, which comprises addingto said motor fuel prior to the formation of gum an aminophenol in whichan amino hydrogen has been substituted by a hydrocarbon radical, Y

in quantity sufiicient to retard such gum formation.

3. The method of preserving a motor fuel containing unsaturated crackedhydrocarbons which normally tend to form gum on storage, which comprisesaddingto said motor fuel prior to the formation of gum apara-aminophenol in which an amino hydrogen has been substituted by ahydrocarbon radical, in quantity suflicient to retard said gumformation.

a. A motor fuel comprising cracked gasoline which normally tends todevelop gums upon storage, to which has been added para-aminophenolaosaeii taining unsaturated cracked hydrocarbons which normally tend toform gum on storage, which comprises adding to said motor fuel prior tothe formation of m an aminophenol in which an amino hydrogen has beensubstituted by a hydrocarbon alkyl radical, in quantity suflicient toretard such gum formation.

"2. A motor fuel comprising cracked gasoline which normally tends todeteriorate and develop gums on storage to which has been added aparaaminophenol in which an amino hydrogen has been substituted by analkyl radical, in quantity suihcient to retardsaid deterioration and gumformation.

8. The method of preserving a motor fuel containing unsaturated crackedhydrocarbons which normally tend to form gum on storage, which comprisesadding to said motor fuel an aminophenol in which both hydrogen atoms ofan amino group have been substituted by alkyl radicals, in quantitysufiicient to retard said gum formation.

9. A motor fuel comprising cracked gasoline which normally tends todevelop gums upon storage, to which has been added para-aminophenol inwhich both amino hydrogens have been sub stituted by alkyl radicals, inquantity sufficient to retard said gum formation.

10. The method of preserving a motor fuel containing unsaturated crackedhydrocarbons which normally tend to form gum on storage, which comprisesadding to said motor fuels a small proportionoi para-dimethylaminophenol, in quantity suficient to retard said gum formation.

11. A motor fuel comprising cracked gasoline which normally tends todeteriorate and develop gums upon storage, to which has been added anaminophenol in which an amino hydrogen has been substituted by anaralkyl radical, in quantity sumcient to retard said gum formation.

12. The method of preserving a motor fuel containing unsaturatedpetroleum hydrocarbons which normally tend to form gum on storage,which-comprises adding to said motor fuel prior to the formation of gum,an aminophenol in which an amino hydrogen has been substituted by anaralkyl hydrocarbon radical, in quantity suflicient to retard said gumformation.

13. A motor fuel comprising cracked gasoline which normally tends todeteriorate and develop gums upon storage, to which has been added priorto the formation of gum, an aminophenol in which an amino hydrogen hasbeen substituted by a benzyl radical, in quantity suiflcient to retardsaid gum formation.

14. A motor fuel comprising unsaturated cracked gasoline which normallytends to form gum and deteriorate in anti-'knock value on storage, towhich has been added a para-aminophenol in which an amino hydrogen hasbeen substituted by a benzyl radical, in quantity sufiiclent to retardgum formation therein.

15. A motor fuel comprising cracked gasoline which normally tends todeteriorate and develop gums upon storage, to which has been addedpara-benzyl aminophenol, in quantity suflicient to retard said gumformation.

16. The method of treating a liquid motor fuel comprising unsaturatedhydrocarbons which normally tend to form gum on storage, which comprisesincorporating in said motor fuel prior to the formation of gumpara-benzyl aminophenol in quantity suflicient to retard gum formationtherein.

17. A motor fuel comprising cracked hydrocarbon distillates whichnormally tend to deteriorate and develop gummy substances upon storageand an aminocresol in which an amino hydro- 15 gen has been substitutedby a hydrocarbon radi cal, in quantity sumcient to retard said gumformation.

18. The method of preserving a motor fuel containing unsaturated crackedhydrocarbons which normally tend to form gum on storage, which comprisesadding to said motor fuel prior to the formation of gum a. benzylaminocresol, in quantity suflicient to retard said gum formation.

19. A motor fuel comprising cracked gasoline which normally tends todeteriorate and develop gums upon storage, to which has been added 5-benzylamin0-2-cres0l, in quantity sufiicient to retard said gumformation.

HARRY T. BENNETT. LE ROY G. STORY.

